Upcoming Events

Toast to the last days of summer with lively waterfront fun! Friday | 3 to 6 pm: Champagne and Oysters paired with live music to set the perfect tone. Saturday | 12 to 4 pm: Tacos and Margarita Bar featuring Sangria and our exclusive Dobel Inn at Perry Cabin Single Barrel Tequila. Sunday | 2 to 5 pm: Bubbles, small bites, and live music to close out the weekend.  It’s the farewell to summer you didn’t know you needed.

Join us every Friday in September and October from 3–6 PM for an afternoon of live music by the water! Relax into the weekend with stunning waterfront views, small bites, and crisp, refreshing drinks in hand. Soak up the golden light of falls arrival as it dances across the river— good vibes, great company, and a front-row seat to the season’s beauty.

Join us for a weekend under the stars September 27–28, led by Sky Guy Greg Redfern, NASA JPL Solar System Ambassador. Experience expert-led presentations, stunning telescope viewings, and unforgettable waterside stargazing sessions. Whether you’re an avid stargazer or simply curious about the night sky, this immersive event offers something for everyone. View the two-day itinerary here.

The prestigious Chesapeake Film Festival returns to Easton, Maryland from October 10th - 12th! Immerse yourself in the magic of cinema with a captivating lineup of acclaimed films, thought-provoking documentaries, and engaging discussions with industry experts.

Fall into the enchantment of St. Michaels October 17 - 19! Experience the charm of our scenic town as it comes alive with scarecrow contests, pumpkin pie eating competitions, and pumpkin carving festivities scattered throughout. Immerse yourself in the vibrant spirit of the season as you wander the streets adorned with whimsical creations.

Get ready to indulge in the flavors of the Chesapeake Bay's favorite fall festival! Join us for Chesapeake Bay Maritime Museum’s Oyster Fest on Saturday, October 25th for a day filled with live music, exciting retriever demonstrations, and of course, mouthwatering oysters and more. Sip on local brews, slurp down freshly shucked oysters, and savor the taste of autumn by the bay. It's an event you won't want to miss!

Experience the charm of the Eastern Shore at Easton's Waterfowl Festival, taking place from November 14th - 16th! Delight in a weekend filled with exquisite art collections, culinary delights, and the authentic ambiance of the Chesapeake Bay. Immerse yourself in the rich tradition of waterfowl calling and witness captivating live demonstrations. Don't miss this true Eastern Shore classic, where art, culture, and nature converge for an unforgettable celebration!

Mark your calendar for November 22nd, as the Chesapeake Bay Maritime Museum in St. Michaels, Maryland, hosts the Holiday Edition of the beloved Sea Glass and Coastal Arts Festival. This seasonal celebration will showcase coastal craftsmanship at its finest, with over 90 exhibitors offering unique jewelry, home décor, art, and more—just in time for the holidays.

Join us on Friday, November 28th for the beloved Lighting of the Lane, a cherished tradition that warmly welcomes the holiday season. Guests of the Inn are invited to step into a winter wonderland where snowflakes dance, Santa spreads cheer, and cozy beverages are enjoyed as we count down to the grand unveiling of lights along the lane.

Step into the magic of Midnight Madness the first weekend of December in St. Michaels. Our charming shops extend their hours, welcoming you with festive refreshments, delectable snacks, and exclusive sales. Every purchase at participating businesses brings you closer to winning delightful gift baskets, adding to the joy of the season.

Experience the magic of Christmas in St. Michaels from December 12 - 14! Join us for a weekend filled with joyous celebrations as our picturesque town comes alive with holiday spirit. Don't miss the enchanting Talbot Street Christmas Parade and the dazzling Lighted Boat Parade, where the waterfront sparkles with festive cheer. Throughout the town, discover a plethora of merry festivities to delight in with loved ones amidst the festive atmosphere of Christmas in St. Michaels.